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GB2051831B - Fluorinated copolymers and cation exchange membrane and process for producing the same - Google Patents

Fluorinated copolymers and cation exchange membrane and process for producing the same

Info

Publication number
GB2051831B
GB2051831B GB8017804A GB8017804A GB2051831B GB 2051831 B GB2051831 B GB 2051831B GB 8017804 A GB8017804 A GB 8017804A GB 8017804 A GB8017804 A GB 8017804A GB 2051831 B GB2051831 B GB 2051831B
Authority
GB
United Kingdom
Prior art keywords
membrane
cation exchange
acid groups
fluorinated
exchange membrane
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB8017804A
Other versions
GB2051831A (en
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Asahi Kasei Corp
Asahi Chemical Industry Co Ltd
Original Assignee
Asahi Chemical Industry Co Ltd
Asahi Kasei Kogyo KK
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from JP54067888A external-priority patent/JPS6045653B2/en
Priority claimed from JP6788979A external-priority patent/JPS55160007A/en
Priority claimed from JP54085852A external-priority patent/JPS5910658B2/en
Priority claimed from JP9030179A external-priority patent/JPS5912116B2/en
Priority claimed from JP9030279A external-priority patent/JPS5616460A/en
Priority claimed from JP54165675A external-priority patent/JPS5911581B2/en
Priority claimed from JP16817979A external-priority patent/JPS5911582B2/en
Priority claimed from JP17031579A external-priority patent/JPS55160008A/en
Application filed by Asahi Chemical Industry Co Ltd, Asahi Kasei Kogyo KK filed Critical Asahi Chemical Industry Co Ltd
Publication of GB2051831A publication Critical patent/GB2051831A/en
Publication of GB2051831B publication Critical patent/GB2051831B/en
Application granted granted Critical
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C313/00—Sulfinic acids; Sulfenic acids; Halides, esters or anhydrides thereof; Amides of sulfinic or sulfenic acids, i.e. compounds having singly-bound oxygen atoms of sulfinic or sulfenic groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C313/02—Sulfinic acids; Derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/78—Halides of sulfonic acids
    • C07C309/79—Halides of sulfonic acids having halosulfonyl groups bound to acyclic carbon atoms
    • C07C309/82—Halides of sulfonic acids having halosulfonyl groups bound to acyclic carbon atoms of a carbon skeleton substituted by singly-bound oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/78—Halides of sulfonic acids
    • C07C309/79—Halides of sulfonic acids having halosulfonyl groups bound to acyclic carbon atoms
    • C07C309/84—Halides of sulfonic acids having halosulfonyl groups bound to acyclic carbon atoms of a carbon skeleton substituted by carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/16—Sulfones; Sulfoxides having sulfone or sulfoxide groups and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C317/18—Sulfones; Sulfoxides having sulfone or sulfoxide groups and singly-bound oxygen atoms bound to the same carbon skeleton with sulfone or sulfoxide groups bound to acyclic carbon atoms of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/10—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C323/11—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/12—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D327/00—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms
    • C07D327/02—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms one oxygen atom and one sulfur atom
    • C07D327/04—Five-membered rings
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F214/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen
    • C08F214/18—Monomers containing fluorine
    • C08F214/184—Monomers containing fluorine with fluorinated vinyl ethers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00—Chemical modification by after-treatment
    • C08F8/04—Reduction, e.g. hydrogenation
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F8/00—Chemical modification by after-treatment
    • C08F8/12—Hydrolysis
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
    • C08J5/20—Manufacture of shaped structures of ion-exchange resins
    • C08J5/22—Films, membranes or diaphragms
    • C08J5/2206—Films, membranes or diaphragms based on organic and/or inorganic macromolecular compounds
    • C08J5/2218—Synthetic macromolecular compounds
    • C08J5/2231—Synthetic macromolecular compounds based on macromolecular compounds obtained by reactions involving unsaturated carbon-to-carbon bonds
    • C08J5/2237—Synthetic macromolecular compounds based on macromolecular compounds obtained by reactions involving unsaturated carbon-to-carbon bonds containing fluorine
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F216/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal or ketal radical
    • C08F216/12—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal or ketal radical by an ether radical
    • C08F216/14—Monomers containing only one unsaturated aliphatic radical
    • C08F216/1466—Monomers containing sulfur
    • C08F216/1475—Monomers containing sulfur and oxygen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2327/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Derivatives of such polymers
    • C08J2327/02—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Derivatives of such polymers not modified by chemical after-treatment
    • C08J2327/12—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Derivatives of such polymers not modified by chemical after-treatment containing fluorine atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Manufacturing & Machinery (AREA)
  • General Chemical & Material Sciences (AREA)
  • Materials Engineering (AREA)
  • Inorganic Chemistry (AREA)
  • Manufacture Of Macromolecular Shaped Articles (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

There is presented a novel fluorinated cation exchange membrane containing carboxylic acid groups and sulfonic acid groups, both in the form of a specific pendant structure, the carboxylic acid groups being at least 20% on one surface of the membrane and gradually decreasing toward the innerside of the membrane, which membrane is useful in electrolysis of an aqueous alkali metal halide solution. The membrane can be prepared from a novel copolymer of a fluorinated olefin with a novel sulfur containing fluorinated vinylether of the formula: <IMAGE> wherein k is 0 or 1, l is an integer of 3 to 5, Z is -S- or -SO2- and R is C1-C10 alkyl, an aryl, Cl or C1-C10 perfluoroalkyl, by treatment of a membrane of the polymer with a selected reducing agent.
GB8017804A 1979-05-31 1980-05-30 Fluorinated copolymers and cation exchange membrane and process for producing the same Expired GB2051831B (en)

Applications Claiming Priority (8)

Application Number Priority Date Filing Date Title
JP6788979A JPS55160007A (en) 1979-05-31 1979-05-31 Novel fluorinated copolymer and production thereof
JP54067888A JPS6045653B2 (en) 1979-05-31 1979-05-31 Novel fluorinated cation exchange membrane and its manufacturing method
JP54085852A JPS5910658B2 (en) 1979-07-09 1979-07-09 Novel fluorinated vinyl ether compound and its production method
JP9030279A JPS5616460A (en) 1979-07-18 1979-07-18 Novel fluorinated carboxylic acid derivative and its preparation
JP9030179A JPS5912116B2 (en) 1979-07-18 1979-07-18 Novel fluorinated acid fluoride and its production method
JP54165675A JPS5911581B2 (en) 1979-12-21 1979-12-21 Fluorinated vinyl ether compound and its production method
JP16817979A JPS5911582B2 (en) 1979-12-26 1979-12-26 Fluorinated acid fluoride and its manufacturing method
JP17031579A JPS55160008A (en) 1979-12-28 1979-12-28 Fluorinated copolymer and production thereof

Publications (2)

Publication Number Publication Date
GB2051831A GB2051831A (en) 1981-01-21
GB2051831B true GB2051831B (en) 1983-06-08

Family

ID=27572595

Family Applications (4)

Application Number Title Priority Date Filing Date
GB8017838A Expired GB2053902B (en) 1979-05-31 1980-05-30 Fluorinated compounds
GB08221499A Expired GB2123812B (en) 1979-05-31 1980-05-30 Fluorinated carboxylic acids and derivatives their production and their use to produce fluorinated acid fluorides
GB8017804A Expired GB2051831B (en) 1979-05-31 1980-05-30 Fluorinated copolymers and cation exchange membrane and process for producing the same
GB08221735A Expired GB2118541B (en) 1979-05-31 1982-07-27 Fluorinated vinyl ethers and their preparation

Family Applications Before (2)

Application Number Title Priority Date Filing Date
GB8017838A Expired GB2053902B (en) 1979-05-31 1980-05-30 Fluorinated compounds
GB08221499A Expired GB2123812B (en) 1979-05-31 1980-05-30 Fluorinated carboxylic acids and derivatives their production and their use to produce fluorinated acid fluorides

Family Applications After (1)

Application Number Title Priority Date Filing Date
GB08221735A Expired GB2118541B (en) 1979-05-31 1982-07-27 Fluorinated vinyl ethers and their preparation

Country Status (1)

Country Link
GB (4) GB2053902B (en)

Families Citing this family (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4600774A (en) * 1981-01-30 1986-07-15 Minnesota Mining And Manufacturing Company Cyclic sulfoperfluoroaliphaticcarboxylic acid anhydrides and amide derivatives thereof
US4851161A (en) * 1981-07-02 1989-07-25 E. I. Du Pont De Nemours And Company β-substituted polyfluoropropionate salts and derivatives
US4474700A (en) * 1981-07-02 1984-10-02 E. I. Du Pont DeNemours and Company β-Substituted polyfluoropropionate salts and derivatives
DE3230528A1 (en) * 1982-02-27 1983-09-15 Hoechst Ag, 6230 Frankfurt METHOD FOR THE PRODUCTION OF CARBOXYL GROUPS CONTAINING FLUOROCOLOR POLYMERISATES, SOME STARTING MATERIALS THEREFOR, AND THE FLUORINE SULPHATE COMPOUNDS THAT APPEAR IN THE METHOD
US4576752A (en) * 1982-07-19 1986-03-18 E. I. Du Pont De Nemours And Company β-Substituted polyfluoroethyl compounds
US4766248A (en) * 1982-07-19 1988-08-23 E. I. Du Pont De Nemours And Company β-substituted polyfluoroethyl compounds
US4686300A (en) * 1983-03-07 1987-08-11 E. I. Du Pont De Nemours And Company Polyfluoro gamma-ketoesters and 5-hydroxy gamma lactone analogues thereof
US4526948A (en) * 1983-12-27 1985-07-02 E. I. Du Pont De Nemours And Company Fluorinated vinyl ethers, copolymers thereof, and precursors thereto
US4474899A (en) * 1983-12-27 1984-10-02 E. I. Du Pont De Nemours And Company Process for preparing ester fluorinated ion exchange polymer precursor by acid treatment of ether
EP0192143B1 (en) * 1985-02-09 1996-01-10 Asahi Kasei Kogyo Kabushiki Kaisha Permeable polymer membrane for desiccation of gas
US4940525A (en) * 1987-05-08 1990-07-10 The Dow Chemical Company Low equivalent weight sulfonic fluoropolymers
US5252193A (en) * 1991-11-04 1993-10-12 E. I. Du Pont De Nemours And Company Controlled roughening of reinforced cation exchange membrane
EP0545068A3 (en) * 1991-11-08 1993-12-22 Du Pont Wetting of diaphragms
US5281680A (en) * 1993-01-14 1994-01-25 E. I. Du Pont De Nemours And Company Polymerization of fluorinated copolymers
US5414119A (en) * 1993-03-02 1995-05-09 Shin Etsu Chemical Co., Ltd. Hexafluoropropylene oxide compounds and a method of making same
US5536754A (en) * 1995-02-15 1996-07-16 E. I. Du Pont De Nemours And Company Fluorinated ion-exchange polymers and intermediates therefor
EP1095071B1 (en) * 1998-06-25 2004-06-16 E.I. Dupont De Nemours And Company Aromatic polymers with pendant fluorinated ionic groups
US6624328B1 (en) * 2002-12-17 2003-09-23 3M Innovative Properties Company Preparation of perfluorinated vinyl ethers having a sulfonyl fluoride end-group
JP4792972B2 (en) 2003-07-02 2011-10-12 旭硝子株式会社 Fluorine-containing sulfonyl fluoride compound
CN100384817C (en) * 2003-07-04 2008-04-30 旭硝子株式会社 Process for production of fluorinated sulfonyl fluorides

Also Published As

Publication number Publication date
GB2118541B (en) 1984-05-16
GB2123812A (en) 1984-02-08
GB2118541A (en) 1983-11-02
GB2123812B (en) 1984-07-18
GB2051831A (en) 1981-01-21
GB2053902B (en) 1984-02-29
GB2053902A (en) 1981-02-11

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Legal Events

Date Code Title Description
PE20 Patent expired after termination of 20 years

Effective date: 20000529